WO2005033165A1 - Dispersion pur a auto-reticulation - Google Patents

Dispersion pur a auto-reticulation Download PDF

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Publication number
WO2005033165A1
WO2005033165A1 PCT/EP2004/010561 EP2004010561W WO2005033165A1 WO 2005033165 A1 WO2005033165 A1 WO 2005033165A1 EP 2004010561 W EP2004010561 W EP 2004010561W WO 2005033165 A1 WO2005033165 A1 WO 2005033165A1
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WO
WIPO (PCT)
Prior art keywords
component
acid
added
polyol
average molecular
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PCT/EP2004/010561
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German (de)
English (en)
Inventor
Jan Mazanek
Jürgen Meixner
Olaf Fleck
Heino Müller
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Bayer Materialscience Ag
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Publication of WO2005033165A1 publication Critical patent/WO2005033165A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic

Definitions

  • the present invention relates to aqueous self-crosslinking PUR dispersions, stoving lacquers produced therefrom and their use in lacquers and paints, in particular in the automotive coating.
  • aqueous self-crosslinking PUR dispersions stoving lacquers produced therefrom and their use in lacquers and paints, in particular in the automotive coating.
  • the importance of water-based paints and coating materials has risen sharply due to ever stricter emission guidelines with regard to the solvents released during paint application.
  • aqueous coating systems are already available for many areas of application, they often cannot achieve the high quality level of conventional, solvent-based coatings in terms of resistance to solvents and chemicals, as well as elasticity and mechanical strength.
  • no polyurethane-based coating compositions to be processed from an aqueous phase have yet become known which sufficiently meet the high requirements of practice in the automotive refinishing.
  • DE-A 40 01 783 deals with special anionically modified aliphatic polyisocyanates
  • DE-A 28 14 815 and EP-A 0 012 348 and EP-A 0 424 697 which describe aqueous stoving enamel binders based on blocked polyisocyanates and organic polyhydroxyl compounds.
  • the paints described in the prior art do not meet all practical requirements, not even with regard to the solids content and the stability of the paints and their reactivity as well as the properties of the coatings produced therefrom, such as surface smoothness and gloss, and in particular with regard to the resistance to solvents and / or pendulum hardness.
  • the object of the present invention was to provide improved aqueous IC stoving systems, the paints based thereon, in particular, having a high solids content, higher reactivity and the coatings, in addition to high surface smoothness and gloss, being supposed to have improved resistance to solvents and / or pendulum hardness.
  • the present invention relates to a process for the preparation of self-crosslinking polyurethane polymers as the basis of such aqueous IC-Einbrerrnsysterne, characterized in that in a first step at least one aromatic Isocyanatko component or a mixture of at least one aromatic, aliphatic and / or cycloaliphatic isocyanate component (A) with an isocyanate group functionality greater than or equal to 2 with an at least difunctional polyol component (B1) of average molecular weight from 62 to 2500, which contains at least one acid-functional compound (C), to form a prepolymer containing isocyanate groups or hydroxyl groups is implemented, then one or more polyol components (B2) with an OH functionality greater than or equal to 1 and optionally an isocyanate component (A '), which may be the same or different from (A), are added, the resulting NCO-functional Product with a bloc Kierstoff (D) is added so that the isocyanate groups are partially
  • an acid-functional compound (C), which can be the same or different from (C), and an isocyanate component (A "), the same or different from ( A) and (A ') can be added.
  • a ratio of the isocyanate groups, including the blocked groups, to all groups which are reactive toward isocyanates is from 0.5 to 3.0 to 1, preferably 0.6 to 2.0 to 1, particularly preferably 0.8 to 1, 5 to 1 chosen.
  • the present invention likewise relates to the self-crosslinking polyurethane polymers which can be obtained by the process according to the invention, it being essential that at least one aromatic isocyanate is already used to prepare the prepolymer prepared in the first step.
  • Suitable isocyanate components (A), (A '), (A ") are aliphatic, cycloaliphatic, araliphatic and / or aromatic isocyanates with an average functionality of 2 to 5, preferably 2 and with an isocyanate content of 0.5 to 60% -%, preferably from 3 to 40 wt .-%, particularly preferably from 5 to 30 wt .-%, such as toluene diisocyanate (TDI), 2,4-enylmethan dip '' - and / or 4,4-diisocyanate ( MDI) or naphthylene-l, 5-diisocyanate and higher condensed products, tetramethylene diisocyanate, cyclohexane
  • Aromatic polyisocyanates are preferred, particularly preferably tolylene diisocyanate (TDI), diphenylmethane-2,4 'and / or 4,4'-diisocyanate (MDI) and their mixtures with isophorone diisocyanate, bis (4,4-isocyanato-cyclohexylmethane) and hexamethylene diisocyanate.
  • TDI tolylene diisocyanate
  • MDI 4,4'-diisocyanate
  • isophorone diisocyanate bis (4,4-isocyanato-cyclohexylmethane) and hexamethylene diisocyanate.
  • polyisocyanates which contain heteroatoms in the radical containing the isocyanate groups.
  • examples include carbodiimide groups, allophanate groups, isocyanurate groups, urethane groups and biuret groups
  • Polyisocyanates which are particularly preferred in mixtures with aromatic polyisocyanates are those which are mainly used in the production of paints, for example modification products of the above-mentioned simple polyisocyanates containing biuret, isocyanurate or uretdione groups, in particular hexamethylene diisocyanate or isophorone diisocyanate.
  • low molecular weight polyisocyanates containing urethane groups are also suitable, as can be obtained by reacting excess TDI or MDI with simple polyhydric alcohols in the molecular weight range 62 to 300, in particular with trimethylolpropane or glycerol.
  • Suitable polyisocyanates are furthermore the known prepolymers containing terminal isocyanate groups, as are accessible in particular by reacting the simple polyisocyanates mentioned above, especially diisocyanates, with inadequate amounts of organic compounds having at least two functional groups which are reactive toward isocyanates.
  • the ratio of isocyanate groups to hydrogen atoms reactive towards NGO corresponds to 1.05: 1 to 10: 1, preferably 1.5: 1 to 4: 1, the hydrogen atoms preferably originating from hydroxyl groups.
  • NCO prepolymers The type and proportions of the starting materials used in the production of NCO prepolymers are chosen such that the NCO prepolymers preferably have an average NCO functionality of 2 to 3 and a number average molecular weight of 500 to 10,000, preferably 800 to 40O.
  • polyisocyanates for the purposes of the invention are those polymers containing polyurethane, polyester and / or polyacrylate which contain free isocyanate groups and, if appropriate, mixtures thereof, in which only a part of the free isocyanate groups is blocked with the blocking agents, while the remaining part is reacted with an excess of hydroxyl-containing polyesters, polyurethanes and / or polyacrylates and, if appropriate, their mixtures, so that a free hydroxyl-containing polymer is formed which, when heated to suitable baking temperatures, crosslinks without the addition of further groups which are reactive towards isocyanate groups (self-crosslinking one-component baking systems).
  • the polyol component (B1) contains 2- to ⁇ -valent polyol components with a molecular weight of 62 to 2500, preferably 62 to 1000, particularly preferably 62 to 500, at least one of these components being an acid-functional compound (C).
  • Preferred polyol components are, for example, 1,4- and / or 1-3-butanediol, 1,6-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane, polyester and / or polyether polyols of average molecular weight of less or equal to 1000.
  • the polyol component (B1) preferably contains more than 50% by volume of an acid-functional compound (C), particularly preferably the component (B1) contains exclusively compound (C), very particularly preferably only dimethylolpropionic acid.
  • Suitable acid-functional compounds (C) / (C) are hydroxy-functional carboxylic acids and / or sulfonic acids, preferably mono- and dihydroxycarboxylic acids, such as e.g. 2-hydroxyacetic acid, 3-hydroxy ⁇ ropanoic acid and 12-hydroxy-9-octadecanoic acid (ricinoleic acid).
  • Particularly preferred carboxylic acids (C) / (C) are those in which the carboxyl group is prevented from reacting due to steric effects, e.g. Lactic acid.
  • 3-Hydroxy-2,2-dimethylpropanoic acid (hydroxypivalic acid) and dimethylolpropionic acid are very particularly preferred.
  • the polyol component (B2) is selected from the group of
  • linear difunctional polyols with average molecular weights from 300 to 4000, preferably from 300 to 2000, particularly preferably from 300 to 1000,
  • Suitable polyol components (b1) are 2- to 6-valent alcohols and / or mixtures thereof which have no ester groups. Typical examples are ethanediol-1,2, propanediol-1,2 and -1,3, butanediol-1,4, -1,2 or -2,3, hexanediol-1,6, 1,4-dihydroxycyclohexane, glycerol, Trimethylolethane, trimethylolpropane, pentaerythritol and sorbitol. Of course, alcohols with ionic groups or groups which can be converted into ionic groups can also be used as component bl).
  • 1,4- or 1,3-butanediol, 1,6-hexanediol and / or trimethylolpropane are preferred.
  • Suitable linear difunctional polyols (b2) are selected from the group of polyethers, polyesters and / or polycarbonates.
  • the polyol component (b2) preferably contains at least one diol containing ester groups in the molecular weight range from 350 to 4000, preferably from 350 to 2000, particularly preferably from 350 to 1000. This is the average molecular weight which can be calculated from the hydroxyl number.
  • the ester diols are mixtures in which individual constituents which have a molecular weight below or above these limits can also be present in minor amounts. These are the polyester diols known per se, which are composed of diols and dicarboxylic acids.
  • Suitable diols are, for example, 1,4-dimethylol-cyclohexane, 1,4- or 1,3-butanediol, 1,6-hexanediol, neopentyl glycol, 2,2,4-trimethyl-l, 3-pentanediol trimethylolpropane and pentaerythritol or mixtures such diols.
  • Suitable dicarboxylic acids are, will find the preferred use, for example, aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid, cycloaliphatic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, endomethylene tetrahydrophthalic acid and their anhydrides and aliphatic dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid or their anhydrides. Polyester diols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid are preferably used as component (b2).
  • component (b2) are polycaprolactone diols in the average molecular weight range from 350 to 4000, preferably from 350 to 2000, particularly preferably from 350 to 1000, which are used in a manner known per se from a diol or diol mixture of the type mentioned above as starters and ⁇ -caprolactone have been produced.
  • the preferred starter molecule is 1,6-hexanediol.
  • Those polycaprolactone diols which have been prepared by polymerizing ⁇ -caprolactone using 1,6-hexanediol as starters are very particularly preferred.
  • (Co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran can also be used as the linear polyol component (b2).
  • hydroxyl-containing polycarbonates preferably an average molecular weight of 400 to 2000, such as Hexane diol.
  • Suitable monofunctional linear polyethers are e.g. (Co) polyether from ethylene oxide and / or propylene oxide. Monoalkoriol-started polyalkylene oxide polyethers with an average molecular weight of 350 to 2500 and at least 70% ethylene oxide units are preferred. (Co) polymers with more than 75% ethylene oxide units and a molecular weight of 300 to 2500, preferably 500 to 1000, are particularly preferred. Monofunctional alcohols having 1 to 6 carbon atoms are preferably used as starter molecules in the preparation of these polyethers.
  • Suitable polyols (B3) are polyols with an OF ⁇ functionality greater than or equal to 2 and with average molecular weights from 300 to 5000, preferably from 300 to 3000, particularly preferably from 300 to 2000.
  • Preferred polyols (B3) are e.g. Polyethers with an average molecular weight of 300 to 2000 and an average functionality of 2.5 to 4 OH molecules. Polyesters with average OH functionality of 2.5 to 4.0 are also preferred. Suitable diols and dicarboxylic acids for the polyesters are those mentioned under component (b2), but they additionally contain tri- to hexafunctional short-chain polyols, such as e.g. Trimethylolpropane, pentaerythritol or sorbitol. It is preferred to use polyester polyols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid. Mixtures of different polyols or mixtures of diols and triols can also be used.
  • component (B3) are (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran with an average functionality of greater than 2, as well as branched polycarbonates.
  • Non-functional blocking agents can be used as blocking agents (D), e.g. ⁇ -caprolactam, diethyl malonate, ethyl acetoacetate, oximes such as butanone oxime, diisopropylamine, dimethylpyrazole, triazole or mixtures thereof.
  • oximes such as butanone oxime, diisopropylamine, dimethylpyrazole, triazole or mixtures thereof.
  • e-caprolactarn, butanone oxime, diisopropylarnine, 3,5-dimethylpyrazoL triazole and / or mixtures thereof are preferred.
  • component (A) with (B1) to form OH- or NCO-functional prepolymers is of particular importance for the process according to the invention.
  • This implementation should be up front All other components are added. If necessary, further isocyanate (A ') or (A ") should also be used after the prepolymer has been prepared.
  • the prepolymer can be prepared in the same reactor as the reaction with the other components to give the dispersions of the invention The process should be carried out in such a way that when components (A) and (Bl) are converted according to the theoretical stoichiometric equation, there is as little as possible of unconverted excess components (A) and / or (Bl).
  • component (A) is reacted with component (B1), which contains at least one acid-functional compound (C), to form an NCO-functional or OH-furcation prepolymer, then the Components (b1), (b2) and (b3) and optionally the isocyanate component (A '), which may be the same or different from (A), are added, the resulting NCO-functional product with a blocking agent (D) partially blocked and a polyol component (B3) is added in a further stage.
  • Particularly preferred in a last stage is an acid-functional compound (C), which may be the same or different from (C), and an isocyanate component (A "), which may be the same or different from (A) and (A '), added.
  • aqueous dispersions containing the self-crosslinking polyurethanes according to the invention are produced next by methods of the prior art.
  • At least 50%, preferably 80% to 120%, particularly preferably 95 to 105% of the carboxylic acid groups present in the polyurethanes according to the invention are neutralized with suitable neutralizing agents and then dispersed with deionized water.
  • the neutralization can take place before, during or after the dispersing or dissolving step. However, neutralization before adding water is preferred.
  • Suitable neutralizing agents are, for example, triethylamine, dimethylaminoethanol, dimethylcyclohexylamine, triethanolamine, methyldiethanolamine, diisopropanolamine, ethyldiisopropylamm, diisopropylcyclohexylamine, N-methylmorpholine, 2-amino-2-methyl-1-propanol, ammonia or other common neutralizing agents.
  • Amines such as triethylamine, ethyl diisopropylamine, diisopropylhexylamine, dimethylethanolamine is particularly preferred.
  • the present invention also relates to aqueous dispersions containing the self-crosslinking polyurethanes according to the invention. These aqueous dispersions are used as aqueous one-component stoving systems.
  • solvents can optionally also be added to the reaction mixture.
  • All known paint solvents such as N-methylpyrrolidone, methoxypropyl acetate or xylene are suitable. They are preferably used in amounts of 0 to 10% by weight, preferably 0 to 5% by weight. The solvent is' preferably added during the polymerization.
  • the dispersions containing the polyurethanes according to the invention are used as one-component baking systems containing free hydroxyl groups for the production of lacquers, paints and other formulations.
  • Any auxiliary agents and additives used in coating technology, such as pigments, leveling agents, anti-bubble additives or catalysts, can also be added to the aqueous dispersions containing the polyurethanes according to the invention.
  • the invention also relates to the use of the dispersions containing the polyurethanes according to the invention for the production of paints, lacquers or adhesives.
  • the aqueous one-component coating compositions containing the polyurethanes according to the invention can be applied to any heat-resistant substrate in one or more layers by any methods of coating technology, such as spraying, brushing, dipping, flooding or with the aid of rollers and doctor blades.
  • the paint films generally have a dry layer thickness of 0.001 to 0.3 mm.
  • Suitable substrates are, for example, metal, plastic, wood or glass.
  • the coating film is cured at 80 to 220 ° C, preferably at 120 to 180 ° C.
  • aqueous one-component coating compositions containing the polyurethanes according to the invention are preferably suitable for the production of coatings and coatings on steel sheets, as are used, for example, for the production of vehicle bodies, machines, linings, drums or containers.
  • the use of aqueous one-component coating compositions containing the polyurethanes according to the invention is particularly preferred for the production of automotive fillers and / or topcoats and / or primers.
  • Desmodur ® 44 flakes 4,4'-diisocyanatodiphenylmethane
  • Desmodur ® T80 mixture of 80% 1,4- and 20% 1,6-diisocyanatotoluene
  • Desmodur ® Z 4470 Mix trimer of isophorone diisocyanate , 70% in methoxypropylacetate / xylene
  • reaction mixture contained 1.18 eq OH kg.
  • the dispersion obtained had the following properties: solids content: 49.8%
  • Viscosity (rotational viscometer): 2750 mPas
  • the dispersion obtained had the following properties: Solids content: 49.4% viscosity (Haake-Rotavisco, 23 ° C): 660 mPas particle size (LKS): 35 nm
  • the dispersion obtained had the following properties: Solids content: 49.7% viscosity (23 ° C., Haake-Rotavisco): 670 mPas
  • the dispersion had the following properties: Solids content: 48.2% viscosity (23 ° C., Haake-Rotavisco): 410 mPas Particle size (LKS): 31 nm
  • the reaction mixture was cooled to 50 ° C and there were 143.55 g (1.65 Val NGO) Desmodur ® T 80, 210.00 g (0.25 mole) of a polyester of adipic acid and 1,6-hexanediol average molecular weight of 840, 25.00 g (0.05 mol) of a methanol-started polyethylene oxide with an average molecular weight of 500 were added and the mixture was stirred at 50 ° C. until an NCO value of 6.40% (calculated 7.37%) was reached (140 minutes).
  • the dispersion obtained had the following properties: solids content: 46.3%
  • Viscosity (23 ° C, rotary viscometer): 600 mPas particle size (LKS): 180 nm
  • Example 3 The procedure was as described in Example 3, but instead of the compound from Example 1 164.60 g (0.2 eq OH) compound from Example 2 and instead of Desmodur 44 183.50 g (1.75 eq NCO) isophorone diisocyanate was used ,
  • the dispersion obtained had the following properties:
  • Example 4 The procedure was as described in Example 4, but instead of the compound from Example 1 164.60 g (0.2 eq OH) of the compound from Example 2 and instead of Desmodur 44 183.5 g (1.65 eq NCO) isophorone diisocyanate used.
  • the dispersion obtained had the following properties: solids content: 52.9%
  • Viscosity 23 ° C Haake Rotavisco: 2950 mPas particle size (LKS): 118 nm
  • the pendulum hardness is higher and / or the solvent resistance (solubility) is significantly better.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des dispersions PUR aqueuses à auto-réticulation, des laques à cuire produites à partir de ces dispersions, et leur utilisation dans des laques et des peintures, en particulier pour le laquage automobile.
PCT/EP2004/010561 2003-10-02 2004-09-21 Dispersion pur a auto-reticulation WO2005033165A1 (fr)

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DE10346548A DE10346548A1 (de) 2003-10-02 2003-10-02 Selbstvernetzende PUR-Dispersionen
DE10346548.0 2003-10-02

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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005030225A1 (de) * 2005-06-29 2007-01-04 Bayer Materialscience Ag Selbstvernetzende PUR-Dispersionen
DE102005036654A1 (de) * 2005-08-04 2007-02-15 Bayer Materialscience Ag Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur
DE102006021728A1 (de) * 2006-05-09 2007-11-15 Bayer Materialscience Ag Wässrige Dispersionen mit bimodaler Teilchengrößenverteilung
DE102006059680A1 (de) * 2006-12-18 2008-06-19 Bayer Materialscience Ag Colöserfreie, selbstvernetzende PUR-Dispersionen
EP2287260A1 (fr) * 2009-07-02 2011-02-23 Bayer MaterialScience AG Dispersion de polyuréthane réticulable

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EP0576952A2 (fr) * 1992-07-03 1994-01-05 Bayer Ag Compositions dispersables de polyisocyanates solubles dans l'eau et leur utilisation dans des vernis au four
DE19930555C1 (de) * 1999-07-02 2001-01-18 Basf Coatings Ag Wäßriger Beschichtungsstoff, insbesondere wäßriger Füller oder Steinschlagschutzgrund
DE10032977A1 (de) * 2000-07-06 2002-01-24 Basf Coatings Ag Beschichtungsstoff und seine Verwendung als Füller oder Steinschlagschutzgrundlack

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DE2456469C2 (de) * 1974-11-29 1983-01-13 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel
US4119602A (en) * 1977-04-07 1978-10-10 W. R. Grace & Co. Aqueous urethane codispersions
US4433017A (en) * 1981-09-17 1984-02-21 Dai-Ichi Kogyo Seiyaku Co., Ltd. Thermally reactive water-soluble blocked urethane prepolymer
DE3828157A1 (de) * 1988-08-19 1990-02-22 Hoechst Ag Verwendung von polyurethanharzen fuer waessrige fuellerzusammensetzungen
DE69026570T2 (de) * 1989-10-03 1996-10-31 Asahi Glass Co Ltd Wässrige Polyurethanzusammensetzung und ihre Verwendung
DE4001783A1 (de) * 1990-01-23 1991-07-25 Bayer Ag Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung als bindemittel fuer ueberzugsmittel oder als reaktionspartner fuer gegenueber isocyanatgruppen oder carboxylgruppen reaktionsfaehige verbindungen
DE10216945A1 (de) * 2002-04-17 2003-11-06 Bayer Ag Selbstvernetzende PUR-Dispersionen

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Publication number Priority date Publication date Assignee Title
EP0576952A2 (fr) * 1992-07-03 1994-01-05 Bayer Ag Compositions dispersables de polyisocyanates solubles dans l'eau et leur utilisation dans des vernis au four
DE19930555C1 (de) * 1999-07-02 2001-01-18 Basf Coatings Ag Wäßriger Beschichtungsstoff, insbesondere wäßriger Füller oder Steinschlagschutzgrund
DE10032977A1 (de) * 2000-07-06 2002-01-24 Basf Coatings Ag Beschichtungsstoff und seine Verwendung als Füller oder Steinschlagschutzgrundlack

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US20050075470A1 (en) 2005-04-07

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